Abstract
Soybean and linseed oils were selectively hydroenated with copper-on-silica gel catalyst. The linolenate content of the oils was reduced to diene and monoene with no appreciable increase in saturates. Hydrogenated soybean oils contained 68–76% monoene, 11–18% diene, 0% conjugated diene and triene, 1–6% conjugatable diene, 0–0.3% conjugatable triene, and 23–40% isolatedtrans double bonds. Hydrogenated linseed oils contained 44–54% monoene, 35–45% diene, 0% conjugated diene and triene, 0–7% conjugatable diene, 0–02% conjugatable triene, and 44–59% isoaltedtrans double bonds. Esters of fatty acids, derived from these selectively hydrogenated oils, were prepared with trimethylolethane, trimethylolpropane, trimethylolbutane, pentaerythritol, ethylene glycol, C18 saturated cyclic alcohols, primary C12–C18 saturated (nC12, nC14, nC16, nC18) alcohol, and primary C16–C18 saturated (nC16, nC18) alcohol blends. Measurements of viscosities and of smoke, flash, and fire points indicate that these esters are possible replacements for sperm oil. Certain of them, after sulfurization, also have potential as extreme pressure lubricant additives.
Similar content being viewed by others
References
Bell, E.W., J.C. Cowan, and L.E. Gast, JAOCS 49:552 (1972).
Koritala, S., and H.J. Dutton, Ibid. 43:556 (1966).
Koritala, S., R.O. Butterfield, and H.J. Dutton, Ibid. 47:266 (1970).
Popescu, O., S. Koritala, and H.J. Dutton, Ibid. 46:97 (1969).
Okkerse, C., A. DeJonge, J.W.E. Coenen, and A. Rozendaal, Ibid. 44:152 (1967).
DeJonge, A., J.W.E. Coenen, and C. Okkerse, Nature 206:373 (1965).
Miyake, R., British Patent 670,906 (1952).
Koritala, S., U.S. Patent 3,515,678.
Koritala, S., JAOCS 49:83 (1972).
Koritala, S., Ibid. 45:197 (1968).
Bell, E.W., J.P. Friedrich, L.E. Gast, and J.C. Cowan, Ibid. 42:876 (1965).
“Official and Tentative Methods of the American Oil Chemists’ Society”, Vol. I, Third edition, AOCS, Champaign, IL, 1964.
Annual Book of Standards American Society for Testing and Materials, Part 17, ASTM, Philadelphia, PA, revised to 1967.
Federal Test Methods Standard No. 791B, U.S. Federal Supply Service, Washington, DC.
Ranney, M.W., “Lubricant Additives,” Noyes Data Corporation, Park Ridge, NJ, 1973.
Author information
Authors and Affiliations
About this article
Cite this article
Bell, E.W., Cowan, J.C., Gast, L.E. et al. Sperm oil replacements from selectively hydrogenated soybean and linseed esters: Special lubricants. J Am Oil Chem Soc 53, 511–517 (1976). https://doi.org/10.1007/BF02636825
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02636825